Acetovanillone → (Z)-1-[4-[(4-chloro-2-butenyl)oxy]-3-methoxyphenyl]ethanone

HRID 2379948Notes

Reaction equation

HRID 2379948 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].[Cl:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]Cl>C(#N)C>[Cl:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][C:6]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 2214AcetovanilloneHCID 11430Potassium CarbonateHCID 64321151,4-Dichloro-cis-2-butene

Product 1

HCID 57454977(Z)-1-[4-[(4-chloro-2-butenyl)oxy]-3-methoxyphenyl]ethanoneYield 10.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 4-hydroxy-3-methoxyacetophenone (16.6 g, 0.1 mole), K2CO3 (14 g, 0.10 mole) and cis-1,4-dichloro-2-butene (Aldrich, 15 g, 0.12 mole) in acetonitrile (250 ml) was heated at reflux for 2.5 hr. The mixture was filtered and concentrated to an oil. Purification was by flash chromatography. The fractions containing the purest product were combined and concentrated to give white crystals, 7.7 g, 30% . This was recrystallized from ether to give analytical pure (Z)-1-[4-[(4-chloro-2-butenyl)oxy]-3-methoxyphenyl]ethanone (2.72 g), m.p.=64°-66° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hr
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated to an oil
  5. customPurification
  6. additionThe fractions containing the purest product
  7. concentrationconcentrated
  8. customto give white crystals, 7.7 g, 30%
  9. customThis was recrystallized from ether

Sources & evidence

ORD record
ord-ad2767c05bff4c4da9981e2e9bc29674
Source dataset
uspto-grants-1994_11
Patent number
US05364866

Reaction notes

Loading…